Sodium Bicarbonate → 1-(4-{1-Ethyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenoxy)-3,3-dimethyl-butan-2-ol

HRID 547076Notes

Reaction equation

HRID 547076 reaction equation
C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].[CH2:15]([C:17]([C:35]1[CH:48]=[CH:47][C:38]([O:39][CH2:40][C:41](=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43])=[C:37]([CH3:49])[CH:36]=1)([C:20]1[CH:25]=[CH:24][C:23]([B:26]2[O:30][C:29]([CH3:32])([CH3:31])[C:28]([CH3:34])([CH3:33])[O:27]2)=[CH:22][CH:21]=1)[CH2:18][CH3:19])[CH3:16].C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:15]([C:17]([C:35]1[CH:48]=[CH:47][C:38]([O:39][CH2:40][CH:41]([OH:46])[C:42]([CH3:45])([CH3:44])[CH3:43])=[C:37]([CH3:49])[CH:36]=1)([C:20]1[CH:25]=[CH:24][C:23]([B:26]2[O:27][C:28]([CH3:33])([CH3:34])[C:29]([CH3:31])([CH3:32])[O:30]2)=[CH:22][CH:21]=1)[CH2:18][CH3:19])[CH3:16]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 3611392Lithium tri-s-butylborohydrideHCID 57443524HCID 57443524, compound

Product 1

HCID 574435301-(4-{1-Ethyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenoxy)-3,3-dimethyl-butan-2-olYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium tri-sec-butylborohydride in tetrahydrofuran (1.06 M, 0.178 mL, 0.189 mmol) was added to a solution of 1-(4-{1-ethyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenoxy)-3,3-dimethyl-butan-2-one (Example 143-(4); 75.2 mg, 0.157 mmol) in tetrahydrofuran (3 mL) at −78° C., and the mixture was stirred for 30 minutes. The reaction mixture was then poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1) to give the target compound as a colorless oil (46.6 mg, 62%).

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-b64ed16a644c4628ba6a054020e6fc11
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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